Beta-hydroxy protected didecyl quaternary ammonium salt with anticancer activity and preparation method thereof

A double-decyl quaternary ammonium salt and hydroxyl protection technology, which is applied in the field of synthesis of emodin derivatives, can solve the problems of high toxicity, poor water solubility of emodin, and unclear biological activity mechanism

Inactive Publication Date: 2011-02-09
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, emodin itself has poor water solubility, high toxicity, poor biological activity, and the

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: intermediate product 2 Synthesis of (1,3,8-trimethoxy-6-methyl-9,10-anthraquinone)a

[0024] Get 1.6g (5.8mmol) emodin and dissolve in 120ml acetone, add 12g (87mmol) anhydrous potassium carbonate, slowly add dropwise 8ml (87mmol) of (CH 3 O) 2 SO 2 , Refluxed for 24h, cooled to room temperature, concentrated solution, added 100ml of water and stirred for 30min, suction filtered, washed with a small amount of cold acetone to obtain a yellow powder crude product, separated by silica gel column chromatography to obtain 1.52g of bright yellow solid, yield 82.6%. product structure 1 Confirmed by H NMR, IR, melting point. mid product 2 The characterization data are as follows:

[0025] m.p. 226~228℃; IR(KBr) ν max / cm-1 : 2941,2843,1662,1601,1322,1241,1022,759. 1 HNMR (400MHz, CDCl 3 ), δ : 7.65(s, 1H, Ar-H), 7.34(d, 1H, J =2.4Hz, Ar-H), 7.11(s, 1H, Ar-H), 6.78(d, 1H, J =2.0Hz, Ar-H), 4.00(s, 3H, OCH 3 ), 3.97(s, 3H, OCH 3 ), 3.96(s, 3H, ...

Embodiment 2

[0026] Embodiment 2: intermediate product 2 Synthesis of (1,3,8-trimethoxy-6-methyl-9,10-anthraquinone)b

[0027] Get 1.6g (5.9mmol) emodin and dissolve in 200ml acetone, add 10g (73mmol) anhydrous potassium carbonate, slowly add dropwise 4ml (43mmol) of (CH 3 O) 2 SO 2 , Refluxed for 24h, cooled to room temperature, concentrated solution, added 80ml of water and stirred for 30min, suction filtered, washed with a small amount of cold acetone to obtain a yellow powder crude product, separated by silica gel column chromatography to obtain 1.34g of bright yellow solid, yield 72.8%.

Embodiment 3

[0028] Embodiment 3: intermediate product 2 Synthesis of (1,3,8-trimethoxy-6-methyl-9,10-anthraquinone)c

[0029] Get 1.6g (5.9mmol) emodin and dissolve in 180ml acetone, add 10g (73mmol) anhydrous potassium carbonate, slowly add dropwise 4ml (43mmol) of (CH 3 O) 2 SO 2 , refluxed for 20 h, cooled to room temperature, concentrated solution, added 60 ml of water and stirred for 30 min, filtered with suction, washed with a small amount of cold acetone to obtain a yellow powder crude product, separated by silica gel column chromatography to obtain 1.30 g of bright yellow solid, yield 70.6%.

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Abstract

The invention relates to the synthesis of an emodin derivative with anticancer function, in particular to beta-hydroxy protected didecyl quaternary ammonium salt with anticancer activity and a preparation method thereof. The didecyl quaternary ammonium salt is methyl didecyl-[2-(4,5-dihydroxy-7-methoxy-9,10-anthraquinonyl)methyl] ammonium salt and is prepared from emodin serving as a raw materialthrough a series of synthetic reactions. In the invention, the emodin derivative has proliferation inhibiting functions with different degrees for five cancer cells such as liver cancer HepG2, gastric cancer BGC, neuroma SH-SY5Y, gastric cancer AGS and cervical cancer Hela and the normal human embryonic lung fibroblast HELF, and can be used for preparing medicaments for treating cancers.

Description

technical field [0001] The present invention relates to the synthesis of a class of emodin derivatives with anticancer function, more specifically to a kind of β-hydroxyl protected bidecyl quaternary ammonium salt with anticancer activity and its preparation method. technical background [0002] Emodin is an anthraquinone compound with a high content in Polygonaceae plants, which has various biological activities, such as anti-infection, anti-virus, immunosuppression, liver protection, anti-tumor, inhibition of cell proliferation, induction of cell apoptosis, prevention of Tumor metastasis and inhibition of protein kinases, etc. However, emodin itself has poor water solubility, high toxicity, insufficient biological activity, and the mechanism of biological activity is not very clear, so emodin has not been used in clinical reports. Therefore, it is very necessary to chemically modify emodin to improve anticancer activity. Contents of the invention [0003] The object of...

Claims

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Application Information

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IPC IPC(8): A61P35/00C07C225/24C07C221/00A61K31/14
Inventor 王文峰邵敬伟
Owner FUZHOU UNIV
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